


On My Orders

by AndreaDTX



Series: What's Your Fantasy? [2]
Category: Supernatural
Genre: Aftercare, Anal Fingering, M/M, Mutual Masturbation, Nipple Play, Orgasm Control, Orgasm Delay, Power Play, Sex Toys
Language: English
Status: Completed
Published: 2017-11-26
Updated: 2017-11-26
Packaged: 2019-02-07 07:01:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,657
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12835815
Author URL: https://archiveofourown.org/users/AndreaDTX/pseuds/AndreaDTX
Summary: Sam wants to play and Dean's game for it.Stand-alone.





	On My Orders

**Author's Note:**

> A second piece that's been frolicking through my mind (why, yes, it is fun to think about). Constructive comments and kudos welcome!

For as much as Sam is soft spoken and willing to follow Dean’s lead when they’re out on the hunt, he’s the exact opposite in the bedroom. When it comes to sex, Sam doesn’t want to make love. He wants to fuck. He doesn’t want to seduce or caress. He wants to control and dominate.

Not that Dean's a pushover either, in or out of the bedroom. But he _is_ a hedonist and more than happy to indulge any of Sam’s whims because he knows whatever it is, Sam will make sure that in the end he gets off. _Hard_. So when Sam shyly asks him in the Impala if they can play a game, Dean’s all for it.

Which is how they end up here.

They’re in Sam’s room, a rarity, although Dean isn’t exactly sure why. Maybe Dean’s room is homier, more lived in, like Dean unconsciously wants the space to be welcoming. But if that’s the truth, then being here is Sam’s way of emphasizing that Dean no longer has the home field advantage. This is Sam’s turf and they’re playing by Sam’s rules.

Sam and Dean are standing face to face, a few feet apart, both fully dressed for the day even though they plan to stay in the bunker, save for an emergency. Dean’s fidgeting, flexing and releasing various joints, listening to them pop as he waits for Sam to make the first move.

“Be still.” Sam orders with a smirk. Bastard. He knows that outside of a hunting, motionless is almost impossible for Dean who moves even in his sleep. Judging by the growing bulge at the front of his pants, Sam’s getting more than a little kick out of this.

Playing along, Dean snaps to attention, the way that was drilled into him long ago. Sam watches, appraising, silent. Finally, he speaks.

“If there’s an order you can’t—or won’t-- follow, just say the magic word.”

Flagstaff. The magical phrase that means _“Sammy, stop what you’re doing. We gotta talk about this.”_

“Follow my _exact_ orders. Don’t assume you have permission to make the next move, even if you know what it logically should be. When in doubt, stay where you are or doing what you’re doing. Understood?”

Dean swallows against the anticipation, enjoying the unspoken _obey me_ in Sam’s voice more than he’d ever admit. “Yes, Sammy.”

“Excellent. Loose the flannel.” Sam murmurs softly, crossing his arms.

“Sure thing.” Dean strips off the black and white top layer. He starts to let it fall to the floor but realizes that wasn’t part of Sam’s order. “Do you want me to drop it or…”

Sam motions to a chair in the corner. “Toss it over there. The t-shirt, too.”

When Dean is bare chested, he stands and waits. Sam’s eyes roam over Dean’s chest for a long moment before he looks up to give Dean a smile, one that says he likes what he sees. Dean can’t help but preen a little bit. Damn right he likes what he sees.

“Unbuckle your belt. Unbutton the pants, too.”

Dean does as asked, the promise of playtime already sparking tingles low in his groin.

“Pull down your pants. Underwear, too. Wait. Not all the way down. I want them right under the curve of your ass. Make sure your cock is free, too.”

Dean slides the material down til they’re exactly as specified. He gives a bit of a shiver. It’s only a few more inches of skin than he’d been showing before, but somehow, this makes him feel wildly exposed. His stomach muscles clench as he struggles against the urge to cover himself.

The silence falls heavy but Sam seems content to let him stay there for a long moment. He can almost feel Sam’s eyes gliding over his body. Maybe considering what he wants Dean to do next.

More than willing to let Sam have his fun and already sinking into the stillness of the game, Dean startles a bit when Sam’s attention suddenly cuts to the corner—after all, his hunter instincts are never completely off, only idling-- but the urgency is more of a _Eureka!_ than a _put your dick away and prepare to fight!_ Sam’s just going for a chair he keeps there.

He pulls it over, setting it a few feet away from Dean, and sits down, leaving Dean standing half-naked in the middle of the room. Actually, a little more than half-naked, Dean chuckles to himself.

“Turn around, facing away from me.”

Dean shuffles around, not quite hobbled by his pants.

“Bend over and untie your shoes. Loosen the laces, but don’t take your boots off yet.”

He blushes knowing the view he’ll be giving his little brother, but doesn’t hesitate to follow through. He bends at the waist, not at the knees, and loosens the laces on one shoe and then the other. He doesn’t know if he has permission to straighten so he stays there, bent over, knowing Sam’s ever-observant gaze is soaking in every detail. He hears the clink of a belt clasp, the rasp of a zipper, and imagines Sam sitting, staring at him, touching himself. His stomach flutters at the thought.

“You have a really nice asshole. Nice. Tight. Just a shade darker than the skin around it.”

Dean feels the muscle in question clench then release at the compliment, a quick flutter immediately followed by a mad blush rushing farther down his back and maybe across his ass when he realizes what he’s done.

“Thanks?”

Sam chuckles. “You can stand now. Turn and face me.”

Dean shuffles back, steadfastly pretending he can’t feel the prickly burn faded from _both_ sets of cheeks as he makes eye contact once again with Sam, whose pants are open, but still looks fairly put together.

“Kick off your shoes. Jeans, socks, and underwear off. Put them with your shirts.”

When Dean is done, he finds himself completely naked in the middle of the room. He isn’t sure what to do next. Sam has already warned him not to assume he’s free to move. But a life time of training makes the ‘at-ease’ position feel natural. Dean settles, feet spread hip-width apart, hands tucked at the small of his back.

Sam hums appreciatively. “People would pay good money to see this, take pictures, maybe hang them on their wall. I get it all, live and for free.”

“Lucky,” Dean dares to murmur.

“Come here.”

Dean steps closer to Sam and ends up framed between his mile-long legs.

“Hold out your hand.”

When Dean’s palm is in the air, Sam produces a bottle of lube that had been tucked somewhere behind him and squirts a long line into Dean’s hand.

“Play with your cock,” Sam orders. “I want to watch. Make it good.”

Dean closes his palm, rubbing his fingers to warm the lube, blush returning as his hand lowers to his cock. Damn it. He’s too old for the flushing virgin act, but at this rate his cheeks are going to be sore from it tomorrow. And it’s not like he’s ashamed to admit that he masturbates regularly, but it’s something he normally does in the privacy of his bed at night or in the shower in the mornings. Touching himself, so close to Sammy, while his brother watches, studying him like he’s the most interesting thing in the world is both more arousing and more embarrassing than he cares to admit.

Dean starts with a tentative stroke, a loose stroke from the base of his shaft up to just under the head. A few tugs in, he speeds up a bit, and keeps that up until his cock demands a tighter hold. He switches to a rougher grip, a swift up and down that pulls a rumbling groan from his chest. He sinks into the feeling and his mind starts to wander. He thinks about the red head from the bar in Tulsa who could do the trick with her tongue ring. Elise or Elsa? El something who had the prettiest grey eyes and the plumpest pink lips Dean had ever seen and how she used her ankles around his neck to control his movement as they’d fucked. The girl in Waukeegan with the tattoo who’d been double jointed in her—

“Get out of your head,” Sam snaps.

Dean jerks out of his fantasy and looks down at Sam. Who does not look pleased.

“You’re doing this for me. Not you. Me,” Sam says, voice deceptively calm, like the lull in the middle of a storm. “I don’t want you thinking about anyone or anything else but me and the orders I give you. Keep your eyes on me or I’ll find a way to help you focus.”

The threat sends a chill down Dean’s spine. Sam is sadistically creative in his punishments during scenes like this. While it always leads to a mind-blowing orgasm, the path often includes a lot of screams, tears, and exhausted muscles.

Dean determinedly sets his sights on Sam.

It’s intense, staring down into Sam’s eyes as he jerks himself off. Sam has the type of focused stare that makes Dean feel like Sam can see inside him, through him. Can hear his every thought and desire. Dean whimpers, wanting to break the eye contact, but wanting to follow Sam’s order.

“Harder,” Sam demands, as he presses a firm palm to his own cock through his pants, giving it a flat hand grind Dean knows Sam really enjoys. “And rub the head. You’re holding back. Don’t cheat me.”

Dean shifts his hand, moaning at the additional pressure at the tip of his cock. It’s not necessarily how he’d do it if he were alone, but knowing that he’s doing exactly what Sam wants gives it that extra kick that has him sliding towards the edge. Sam stares, refusing to break their eye contact until Dean is squirming, the muscles in his stomach are trembling as he tries to avoid going any further than he has permission.

“Stop.”

Dean pulls his hand away, equal parts reluctant and relieved, and tries to catch his breath, ignoring his cock’s objections to the loss of that oh-so-good slide and tug.

“On the bed. Face up. Knees bent, feet flat on the bed. I want to be able to see everything.”

Dean moves quickly and Sam follows, sitting on his haunches at the foot of the bed. After Dean is in position, Sam stares intently between Dean’s legs long enough to make him fidget just a little before he shifts to reach over Dean’s head and grab a pillow.

“Lift up.” Sam shoves the pillow under Dean’s ass, forcing a convex curve into Dean’s spine. Dean knows from experience this will grant Sam greater visibility of and access to his hole without needing him to flip over onto his belly. He might not have permission to do so but he can’t help but wiggle his hips in anticipation.

Sam picks up the lube from where he’d tossed it on the bed. “Hand.”

Dean presents his hand and receives more slick.

Sam presses Dean’s thighs further apart. “Open yourself up. Start at one finger and work your way up. Keep your eyes on me.”

Dean shivers at the command and his cock jerks. Fucking himself on his fingers while Sammy watches. It’s doubly effective. Sam knows Dean likes having his ass played with but hates to admit it. Usually, Dean is on his hands and knees where he can bury his head and enjoy the pleasure but pretend it’s something else. Anything else. This takes it one step further. Making Dean do it himself. For an audience. So there can be no denying that he both wants and enjoys it.

Evil genius, that kid.

Dean rubs his fingers together just for a few moments before he curls up to slide his hand down to his hole. He starts with his middle finger, groaning as he runs the digit firmly across his entrance. He works the finger in, one knuckle at a time, moaning at the dual sensation of clenching heat around his finger and fullness in his body.

“Shit, I love watching you do this,” Sam says and Dean gets more than a little thrill out of the smoky husk of arousal he hears in Sam’s voice.

Soon Dean is groaning and his body is clenching around three of own fingers. Sam doesn’t maintain eye contact the whole time; he seems more drawn to watching Dean’s hole twitch and spasm, but he periodically checks to make sure Dean’s looking directly at him. Dean moans faintly every time that penetrating stare meets his own.

Dean is trembling and considering a fourth finger when Sam tells him to stop. He slumps in relief. They’ve never gone that far. But he would do it if Sam orders him to.

Sam tugs Dean’s fingers from his body, the first touch since they’ve started this. Dean wants to beg for more, but that’s not what they’re doing. Not this time. Instead, he lays back, listening to his own labored breathing, waiting for his next order.

Sam gets up and pulls something from his night stand. A box. Roughly the size of a shoe box. A regular shoebox, not Sam’s gigantor clodhoppers. Sam bring it back to the bed with him.

“I’m ready to play,” he says. “I’ll give you what I want you to use, you use it how I say. Understood?”

Dean takes a deep breath and has to work hard for it not to sound like a pant. It’s game time. “Yes, Sammy.”

Sam opens the box. Dean can’t see inside of it from his position, which is likely intentional. He rummages around even though there can’t be that many things in the box given its size. It’s a ploy to build the anticipation. And sadly, it’s working. Dean fights not to twitch as he waits.

The first thing Sam pulls out are a pair of wooden clothespins. He drops them on Dean’s sternum.

“Put them on.”

Dean freezes, breaths shallow but loud in the otherwise silent room. Nipple clamps. They’ve never been his thing. He has too much trouble getting past the initial _owsweetfuckthathurts_ to actually enjoy using them. Sam knows that. Dean hesitates for the first time. “You want me to put them on my nipples?”

Sam smiles.

“Unless you can think of a better place to put them,” he says with a not-at-all-subtle glance at Dean’s balls.

Fuck no.

Dean swallows hard, but then slowly opens his mouth and licks at his fingers. The ones that weren’t just up his ass. He uses the spit to rub at the nubs on his chest, plucking at them to get the blood thickening. He blows a cool breath over the now moist points, shivering at the goosebumps that rise as a result. He nervously picks up the first clothespin, almost dropping it, and tries to figure out the best way to do this. Maybe both at the same time? Yeah, he nods to himself and picks up the second clothespin. Like ripping a bandage off. He pinches them open, lines them up, and lets them go, letting them clamp down. Dean hisses at the burn, back arching off the bed as he tries to work through the pain, fist clenching as he fights the urge to snatch them back off.

“I love when you suffer for me,” Sam whispers.

Dean moans and pries his eyes open to look at Sam who is watching him with a look of awe while squeezing himself through his pants with a grip that’s gotta be bordering on painful, showing just how much he enjoys the visual.

Dean hums and twitches until finally he’s able to find an ebb, a position where the pain is bearable.

Sam rears forward on all fours, leaning in for a closer look, head only a few inches off of Dean’s chest, close enough that his warm breath ghosts over Dean’s bound nipples. “I know you don’t really like the clamps. That’s what makes it so hot. You’re doing it because I like seeing you do it.”

Dean moans at the reminder that in this game, he’s just a blow-up doll come to life, acting out Sam’s every fantasy. His cock jerks, but otherwise he’s perfectly still. He’s not sure he can move without the pain flaring back to life.

Sam sits back and pulls out another item out of the box, dropping it on Dean’s stomach. The mere sight of it pulls a groan from Dean.

“Yes, that one,” Sam says with a smirk.

It’s a dildo. A monster of one. They’ve played with it before. It’s intense. A little longer and thicker than either Sam or Dean’s cocks, both of which could be described as ‘above average’. It’s midnight black, with a wide girth that tapers down suddenly near the base, making it hard to accidentally push out. It’s designed to make the user feel stuffed to capacity and to stretch the walls and nestle up against the prostate so that every single vibration is felt to the fullest.

_Fuck._

Sam lubes up the toy and hands it to Dean with a lascivious grin. A small whimper escapes from Dean.

He has to work to get it inside. He’d been loose, but has closed back up some because of all the clenching he did in reaction to the nipple clamps. He has to really focus to open up for the toy. But he does it, not even bothering to hold back his noises, because Sam loves to watch him struggle.

He’s gasping and sweating by the time his hole is snugged around the base of the toy. It’s touching him, pressing everywhere inside and shooting off sparks of _ohmigawdthatsgood_ all up and down his spine. He eases back down to the bed, trying not to jostle anything, and looks to Sam. Sam who has taken off his shirt and fully undone his pants while Dean was distracted and now has a hand inside his own underwear. Dean licks his lips, quickly drawn in to watching the outline of Sam’s knuckles moving as he slowly strokes himself. Dean can barely hold back the offer to help.

“You’re doing so good,” Sam murmurs, voice husky. “But I want more. We’re going to edge you.”

Dean’s mind desperately clings to the word ‘we’re’ even as he bites back a groan at the word ‘edge’. Maybe ‘we’ meant Sam will finally touch him, give him the skin to skin contact he’s starting to crave like air.

But the hope is dashed when Sam pushes the control to the toy into Dean’s left hand and squeezes more lube into Dean’s right.

He wants Dean to edge himself while he watches.

Dean shivers, the mere thought pushing him closer to the finish.

“First level, slow, loose strokes on your cock,” Sam commands. “And don’t forget: you wait for my permission to cum. Understood?”

Dean swallows hard and nods. He squeezes his hand to activate the control. The dildo comes to life, sending a pleasant but mild buzz through him. It feels good but he can’t get off from it. This is doable.

Sam leaves him there for a while, both brothers rubbing themselves, watching each other.

“Next level, same stroke,” Sam says. He shifts off the bed, his back to Dean for the moment as he kicks his pants and underwear off, letting them drop to the floor. He doesn’t seem worried about his command being followed; he knows Dean will obey.

Dean squeezes his hand again, kicking the remote up to the next level. It’s a stronger buzz, one that makes his cock twitch and his toes itch with the desire to curl. He wants to speed up his stroke to get more out of it, but that’s not allowed. He sticks to the slow, loose strokes Sam wants to see, but does nothing to bite back the soft moans that leak out of him.

Sam settles back on his haunches and just watches. A king surveying his kingdom.

Dean’s not sure how long it lasts before Sam allows him to cycle up to the third setting, but when Sam still refuses to let him tighten his stroke or speed up, Dean feels like he’s dying of frustration. The third setting sends vibrations through his entire pelvis. He can feel it in his hole, his cock, his balls, in the pit of his stomach. It’s good but would be oh-so-much-more satisfying if he could really grip and move like he wants to. But Sam says no. So he won’t.

By the time Sam sends him to the fourth and final setting, his body is tight with tension. The vibrations are strong enough that they shove Dean almost painfully to the teetering brink of an orgasm. Where he hangs endlessly. He knows he’d fly over if his grip speeds up even a fraction, if his grip tightens even an iota.

“ _PleaseSamPlease”_ Dean begs, groaning as the teasing temptation of release sharpens even more in his groin.

“Please, what?” Sam asks, sitting up on his haunches. He’s still touching himself. He makes sure Dean is watching and quickens his own strokes, right to the speed Dean is desperately pleading for, taunting him with what he wants but can’t have. “What do you want, Dean?”

“Wanna come,” Dean moans. “Can’t hold on. “

“Yes, you can.”

“Can’t…” Dean whines.

“Then turn it off,” Sam orders.

Dean keens, already mourning the loss of the intense sensations. But he quickly double clicks, completely deactivating the dildo. Because Sam says so.

“Relax. Hands by your head.”

Dean lets his head roll back onto the mattress, his legs flopping open, leaving him spread eagle. Despite his best efforts, he can’t contain the slight involuntary jerks of his hips, thrusting so needily into the air, or his passage clutching and releasing spastically around the toy inside him as if that might give him that extra push he needs. But he forces his body to relax and settles his hands by his head to wait for Sam.

Sam waits until Dean is completely still and then shifts to his hands and knees. He crawls towards and then over Dean, his body hovering but careful not to make any point of contact. When they’re finally face to face, Sam smiles mischievously, an impish look that Dean shouldn’t find nearly as sexy as he does.

“Good boy.” He leans in and gives Dean a kiss that makes Dean’s head spin and pulls a whimper out of him.

The kiss goes on and on until Sam breaks it, shifting closer to Dean, close enough that Dean thinks he may lay on top of him and finally give him the friction he’s been lacking. But it’s just a tease which Dean realizes when he hears a soft ‘Level one’ in his ear and feels fresh lube squeezed into his hand.

They cycle through several times, each escalation and de-escalation leaving Dean sweatier and trembling harder but all the more determined to win Sam’s game. Sam pushes like he wants Dean to lose. That’s how Dean finds himself on level four, grunting, groaning, and swearing.

“ _Sam, please, gotta,”_ Dean pleads, as he grits his teeth. His hand’s barely skimming his cock but even that feels like too much as his ass clenches desperately around the buzzing dildo inside. He can’t keep still and all the movement is making the pain in his nipples flair back to life, which his brain has flipped from really-fucking-painful to holy-fuck-balls-that’s-good, doubling the inundation of his nervous system.

“You can’t until I tell you to,” Sam points out.

“I know, but… please…”

Sam doesn’t respond. Instead, he watches, silent and waiting.

Dean fights and fights but finally he feels it. It’s inevitable. The rubber band is at its breaking point and he either has to stop or let it snap.

He turns to Sam, mouth open to beg, but stops dead by the recognition he sees in Sam’s eyes.

Sam knows.

“Dean. Cum. Now.”

Sam knocks Dean’s hand away and grabs his cock tightly, giving two quick pumps that send Dean howling into orbit. Dean shudders and twitches, nearly convulsing, as Sam strokes him through his orgasm, all the while murmuring filthy, hot nothings to him. Dean grunts and groans, feeling like he’s about to fall apart. And just as Dean thinks he’s about to land, Sam pulls the clothespins off his nipples sending Dean’s cock into another series of smaller but no less intense pulses and spasms.

When Dean finally comes back to himself, he’s nearly wheezing and can do nothing but flop bonelessly on the bed, just barely hanging on to consciousness. The toy is still pulsing softly at level one, but Sam steps in and shuts it off with a quick double squeeze when all Dean can do is give a whining moan and a baleful look at the controller. Sam gives Dean’s barely-hard cock one last, solid squeeze before letting it flop to his stomach.

“Holy fuckballs,” Dean mutters, utterly unable to move.

“Mmm…”Sam hums in agreement.

Dean’s about ready to lose the good fight and conk out when he realizes Sam is shaking, still desperately hard.

“Shit, that’s not fair.” Dean tries to reach for him, but his hand twitches uselessly to the side. “Fuck. Just take what you need, Sammy.”

Sam looks at him for a moment, a soft, vulnerability Dean hasn’t seen the entire time they’ve been playing.

“I’m serious. You earned it.”

Sam climbs on top of Dean and lowers himself until they’re chest to chest. Dean gives a slight hiss as the soft smattering of hair on Sam’s chests scrapes across his used and abused puffy nipples. Sam’s knees are bent, cozied up along Dean's torso. His hard cock is pressed against Dean’s stomach, settling just a bit higher than Dean’s own now-flaccid dick. Sam slides his arms under Dean’s back, pulling him into a relaxed hug, and rests his head own Dean’s shoulder. In a really pervy way, it reminds Dean how Sam used to rest on his chest when they were much younger. That thought is knocked away when Sam’s hips begin to move. He humps into Dean, searching for the friction he needs. As he grinds, his hugging grip gets tighter and tighter, edging on uncomfortable, but Dean would rather be crushed to death than deny this to Sam. Just as Dean starts to feel tingly from having his breathing constricted, Sam shudders, his hips jerking. Hot jets of cum splash across Dean’s stomach to mix with his own, making him moan at the feeling. Sam jerks a few more times with a loud groan before sighing and flopping down onto Dean.

“Can’t breathe,” Dean complains.

Sam sighs again before heaving his weight off of Dean and onto the bed where they both lie, blissing out and enjoying the buzzy afterglow. Finally, when Sam catches his breath he sits up.

“Was it good?” he asks, the words a little slurred.

“Yeah,” Dean says. He has to bite back a groan when Sam pushes his legs open and uses a very firm tug-tug-tug to get the dildo out of his body. His body aches with the emptiness after its gone.

Sam gets up and collects the toys, reboxing everything, and takes them to the bathroom to deposit in the sink for cleaning. He comes back with a wet washcloth he uses to clean first Dean, then himself. When he’s finished, he lays next to Dean, burrowing in, back to being the little spoon, despite his larger size.

 “So did _you_ like it?” Dean asks, uncustomarily uncertain.

Sam barks out a laugh. “Are you kidding me? That was like directing my own personal porn.”

Dean grins, relieved. “Wanna do it again sometime?”

“I’ll tell you when and where.”

**Author's Note:**

> In my mind, Sam is pretty toppy and Dean is a flexible switch. I've gotten request for Bottom Sam, which I'm working on.


End file.
